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2004
Ketones
Q 0350
47- 078
Enzyme Catalyzed Hydroxymethylation of Aromatic Aldehydes with Formaldehyde. Synthesis of Hydroxyacetophenones and (S)-Benzoins. — Benzaldehyde
lyase catalyzes the reaction of aromatic aldehydes (I) with formaldehyde providing
2-hydroxy-1-arylethan-1-one (III) in high yields. The yield of the reaction depends on
substituents on the aldehyde. Fluorine substitution on the ring decreases the yield of the
reaction. Pyridine carbaldehyde also furnished a low yield. In addition, kinetic resolution of rac-benzoin (IV) with formaldehyde in the presence of BAL provides (S)-benzoins with high e.e. and hydroxyketones (V) via C-C bond cleavage and a bond formation reaction. — (DEMIR*, A. S.; AYHAN, P.; IGDIR, A. C.; DUYGU, A. N.;
Tetrahedron 60 (2004) 31, 6509-6512; Dep. Chem., Middle East Tech. Univ.,
TR-06531 Ankara, Turk.; Eng.) — Bartels
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